Trifluoroacetic acid → 3-Cyano-4-[2-methoxy-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 509099Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([S:22]([N:25](CC2C=CC(OC)=CC=2OC)[C:26]2[S:30][N:29]=[CH:28][N:27]=2)(=[O:24])=[O:23])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[O:20][CH3:21])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:22]([NH:25][C:26]2[S:30][N:29]=[CH:28][N:27]=2)(=[O:24])=[O:23])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][C:11]=1[O:20][CH3:21])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Cyano-N-(2,4-dimethoxybenzyl)-4-[2-methoxy-4-(trifluoromethyl)benzyl]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 30, 33.8 mg, 0.056 mmol) was dissolved in dichloromethane (1 mL) and cooled to 0° C. Trifluoroacetic acid (22 μL, 0.28 mmol) was added and the reaction stirred for 3 hours warming slowly to room temperature. The solvent was removed in vacuo and the residue re-dissolved in methanol (˜5 mL). Once again the solvent was removed in vacuo. The material was suspended in methanol (5 mL) and filtered through Celite™. The reaction mixture was concentrated in vacuo and purified by the B-HPLC method to afford the title compound.

Workup

temperaturewarming slowly to room temperature
customThe solvent was removed in vacuo
dissolutionthe residue re-dissolved in methanol (˜5 mL)
customOnce again the solvent was removed in vacuo
filtrationfiltered through Celite™
concentrationThe reaction mixture was concentrated in vacuo
custompurified by the B-HPLC method

Sources & evidence

ORD record: ord-294af7d23f8f4c8680c91e6c4cc4e84f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096558B2

Reaction notes

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